Matchmaker
by pumpkaboo
Summary: Jack had been watching Pitch. Not in a weird stalker kind of way, in a how could I possibly romance this guy into dating me kind of way. Tooth plays matchmaker.
Jack had been watching Pitch. Not in a weird stalker kind of way, in a how could I possibly romance this guy into dating me kind of way.

He had only been doing such activities for two months, not long in the grand scheme of things, but he just happened to see Pitch lurking around the woods and decided that this was a better chance than any that didn't involve breaking into Pitch's lair (again).

He sauntered up, feeling confident, until Pitch looked at him.

"Frost, what do you want?" he asked, boredom lacing his voice.

"Uh..." suddenly he wasn't so confident. "I was just wondering... you free tomorrow?"

He looked at Jack oddly. "You know what? I just might be busy" he replied sarcastically. "What do you think Frost? I can't go anywhere without one of you Guardians following me around."

"So... you don't have plans?"

"No. I don't."

"Okay. How about we do something, y'know?"

"How about we don't."

Jack, being the persistent spirit that he could be, wasn't so quick to back down. "Why not?"

"I really don't think it would be such a great idea. Anyway, I have the feeling that someone else is listening to this conversation. Maybe you should go away before you make a fool out of yourself."

Jack stepped closer to Pitch and kissed his cheek, trying to show his intentions. "I like you, okay? Why won't you just go out with me?"

"You're too childish" he replied, shrugging him off.

Jack wasn't happy, and he was starting to realize how silly this whole thing was. He sighed and shook his head. "You just don't want to be happy." He let the wind take him away, back to the Pole.

...

Aster threw his hands up in desperation. "I mean it Toothie! I saw him with Pitch!"

She sighed. "So? I know that you said that its weird, but... what if it isn't? This just proves that Jack can talk to him! He knows how Pitch feels. Jack was alone for three hundred years."

"I just don't... I don't trust Pitch, and I don't want Jack to get in trouble."

She seemed curious. "Hm... well, why don't we just ask Jack about it? We can confront him. Why Pitch? Hm?"

Aster sighed. "I think Jack knows that one of us was nearby. Pitch hinted at it. I don't know if Jack really took it seriously though."

She nodded, understanding his concerns. "Well, Jack does have a habit of not listening regardless." She sat down. "If the worst comes to the worst, we will just... confront Pitch."

"Hey... that's a great idea! We should just go and see Pitch and ask him what Jack wanted!"

Tooth blinked. "Um... just us? What about North and Sandy?"

"Well, I didn't want Jack getting suspicious."

"Good point. Well, I am sure the two of us can do it. I mean, if Jack can go alone-"

"Thanks Toothie. I owe you."

She nodded. "Big time" she added under her breath, but she knew Aster would have heard it.

Aster tapped his foot and opened up a tunnel. "Let's go, yeah?"

She nodded and they made their way to Burgess, the woods, more specifically.

Pitch was wandering around in the woods, which Tooth thought was odd. He looked around at the both of them. "What are you two doing here? Come to change my mind?"

"What?" Aster asked. "Change your mind about what?"

"Jack... didn't tell you?"

"We came here to see what Jack was talking to you about."

Pitch chuckled. "Why don't you just ask him?"

"Is he here?" Tooth asked.

"No. I haven't seen him. Since this morning" he added for clarity.

Aster nodded. "I know he was with you this morning. What happened?"

"You weren't listening in?"

"No. Just outta earshot."

"Well, he came by to ask me if I wanted to spend some time with him tomorrow, which I politely refused, may I add." He looked at them as though they were just plain irritating.

"Well, is that it?" Tooth asked, wanting to leave already.

"Why did he want to see you tomorrow?" Aster asked.

"Well, your little winter spirit keeps coming to see me. Usually he doesn't do much, per se. More or less he will have a conversation with me, and then he leaves when he finally gets sick of me giving him the cold shoulder."

Tooth frowned. Jack was spending time with Pitch and no one realized it? Something seemed off. Why was this the case? Why would Jack spend so much time with him?

"If I may say so, I think Frost has just discovered romantic feelings" he sneered.

"What? With you?" Aster chuckled, until he caught Tooth's eye. "No... you don't... Jack would-"

She bit her lip. "Its a possibility. I mean, Jack hasn't really known anybody. He knows us, but... we are family to him." She looked at Pitch. "Don't you dare hurt him" she warned.

He sighed. "Frost isn't worth my time."

She frowned. "Aster, let's go."

He nodded. "Okay."

"To the Pole. That is where Jack is."

"You want to talk to him now?"

"Yes." She looked back at Pitch. "Don't think that we-"

"Seriously Tooth, let's leave him alone and see Jack" Aster said, tapping his foot.

...

Jack lounged around in the workshop. He wasn't even in the mood to annoy the yeti's. Or the elves. Usually that would have been a source of amusement for him, but today he just felt deflated. Why couldn't Pitch show the slightest bit of interest in him?

Maybe he thought Jack was unattractive. What was unattractive anyway? Everyone would have their own definitions, right? Just like people may think that Pitch was unattractive.

Jack didn't like thinking about it. It made him feel even more confused about what he was feeling. Assuming that was even possible. He was almost going to leave the Pole and find something to do, someone to annoy, when Tooth and Aster showed up,

"North is in his office."

"We are here to see you, Jack" Tooth said.

Aster nodded.

"Me? What have I done this time?" he joked, but then he realized how serious their faces were and he stopped. What had he done? His eyes widened and he opened his mouth to apologize for whatever thing he had done, when Tooth's expression softened.

"Jack, we were just so worried" she admitted.

"What? What for?"

"Well, Aster saw you talking to Pitch earlier."

He looked at Aster. It all fell into place. Aster would have seen them this morning, rushed to Tooth, and then confronted Pitch. He bit his lip nervously. "So... what did Pitch have to say?"

"How did-?"

"Well, I just gathered that you two would have wanted to know what the full story was, and instead of seeing me and letting me get too defensive, you would have just cut straight to Pitch."

Aster nodded. "Pretty much actually."

Tooth looked at Jack. "Is there something you want to tell us?"

"I think I like him."

Aster nodded. "Pitch was right. He thought you were just understanding romantic feelings."

"Well, yeah... I don't know a lot about this... its weird though. Who'd have thought I'd want to go out with Pitch?" he chuckled.

Tooth chuckled nervously. "Yeah, I know."

Aster looked at her. "Well, what now?"

"I think we should hash out the pros and cons" she decided.

"Okay, cons, he is our enemy, and he goes against everything we do. Pros... wait, there isn't any!"

"Well, if Jack dates him that is a pro, because Jack would be in love."

"But Pitch probably doesn't like him, so that's another con."

Tooth groaned. "Aster-"

"Sorry."

"So, there really isn't any point in falling in love?" Jack asked curiously. "Interesting. All the kids say its the best feeling ever."

The kids, of course, Jamie, Sophie and the gang had all but grown up now. Teenagers now. They were all interested in dating and friends... and they had less time for Jack, which he was okay with because that was what growing up entailed, hence the whole Pitch fixation thing.

"Is this because of the kids?" she asked. "Are you lonely now that Jamie and Sophie are getting older?"

Jack sighed. "Maybe. I don't know. I didn't know falling in love was even possible..."

Tooth smiled. "Well, you know, I don't think this is a bad thing."

Aster looked at her. "Um, how is it not?"

"Well, being in love is great! We should be celebrating, not berating" she smiled.

Jack looked at her. "I know this is a problem, well, who I like is" he sighed. "But... he doesn't like me anyway."

"Did he tell you that?" Tooth asked.

"Pretty much." Jack shrugged. "I don't know. Maybe I am just being..." he chuckled, Pitch had summed it up. "...childish."

"Well, love is a complex thing."

Jack sighed. "Why?"

"Well... I don't know."

"I just want to fall in love and have someone love me... I never knew that I wanted this until recently. Its still the weirdest feeling. I just thought... that being Jack Frost and a Guardian was just it for me." He stood up. "Sorry, I just..." he rubbed his temples. "I really just want to... I don't know. I need more."

"Understandable" said Tooth. "I think that its great that you are in love."

Aster looked at her. "Was this part of the plan?"

She chuckled. "Of course. Jack needs our support, and this is the perfect time! We should all go with him and he can ask Pitch out and if he says no" she smacked her fist into her hand. "Well, I am sure you get the idea" she smiled.

Jack's eyes widened. "Well, um... there is no need for violence, right? And like I said, Pitch isn't interested."

She shrugged. "Well, we will find a way to change his mind. So... what does Pitch like?"

"Fear. And being an asshole" said Aster, not impressed with Tooth's decisions.

"Well, I am sure we can think of something else..." she seemed deep in thought. She smiled. "Keep me posted. I'll see you guys later."

Aster shook his head. "I never know what she is thinking."

Jack nodded. "Same."

...

Tooth felt nervous as she arrived at the Burgess woods. She saw Pitch slinking away into his lair, where she followed him. "Pitch!"

"What are you doing here Toothiana?"

"I want... I need to ask you a question."

He nodded. "Very well."

"Why aren't you interested in Jack?"

"Simple. He is... too good for me."

She was surprised to hear this. "What do you mean?"

"Don't pry. It isn't polite."

She hovered near him. "But Pitch, I think if you are going to reject Jack's advances you better have a good reason, and you have to be honest with him."

He sighed. "Tooth, seriously-"

"Anyway, I think Jack is able to make his own decisions, so, whatever will be will be. Just you be nice to him or you will have me to contend with" she said, poking his chest.

He stepped back. "I understand. But Tooth, hear me out."

"Of course."

"I can't date Jack."

"Why not?"

"It wouldn't be practical for me to date a Guardian. Imagine the slack you would get if someone was to find out Jack was dating the Boogeyman. Seriously-"

"I have thought about it, but love is love, and I don't want to hinder it. Why not give it a try?" she smiled.

He groaned. "Will it get you to leave me alone?" he asked, but she could hear the faintest of humor in his voice.

"Yes" she decided.

He nodded. "Well, tell Jack to be here tomorrow."

She smiled. "Don't you worry." She flew up a little higher. "And Pitch, you are good enough for Jack." With that she flew away.

He felt the strangest feeling fill his body. Did she mean it? Did that mean that the Guardians had all spoken about this... The possibility of a relationship? Jack would have to get their permission, being one of them and all...

He shook his head. There was no point. Jack could do better, and would do better. He had to put his own feelings aside for Jack's sake...

...

Jack was surprised that Tooth had come to see him. After all, she was only at the Pole just over an hour ago.

"Okay, so, I got you a date with Pitch."

"What?" his eyes widened.

"Yep. You just have to go and see him tomorrow."

"Oh no..."

"Jack? What is it?"

"...you didn't assault him again, did you?" he asked, remembering the 'incident' although it was a good ten years ago.

"No... did you want me to?" she asked, confused.

"No! No... but... how?"

"I have my ways. I just hope it all goes well."

He couldn't believe it! Well, really, he couldn't believe that Tooth had gone to so much effort to get him a date.

"Thanks Tooth... I don't even know how to thank you. I mean... you have made me so happy." He hugged her, she quickly reciprocated.

"I just hope it all goes well" she smiled up at him.

He nodded. It was such a scary-crazy thought. He hoped that Pitch would show up... he also hoped that Pitch wouldn't just tell him that he was wasting his time and tell him to leave.

She smiled. "I'll see you later." She left the room.

All Jack could do was grin like an idiot. Tooth had done all that... just for him. He was so happy.

He practically bounced around the Pole for the rest of the night, confusing North. He still had zero idea what was going and decided that Jack had had too many cookies or candy canes.

When morning arrived, Jack was out the door, riding the wind back to Burgess. He liked how familiar it was here. It didn't matter how many years passed or how long it was between visits, he would always love this town,

He decided to walk around the city, since it was still early, before meeting Pitch. He was sure Burgess would never change. It still had such an old feeling to it, even after all these years.

He smiled and made his way into the forest.

"Jack Frost."

He looked around at Pitch and smiled shyly. He couldn't help it.

Pitch stepped closer, but he didn't look annoyed or angry for once. It was calm. Understanding. "Jack, you're very persistent."

"I know. But I had no idea Tooth was coming to see you."

"I know. She might be a little more persistent than you. So..."

"What did Tooth say to you?"

"She just nagged me a little. Just being herself really."

Jack chuckled. "Aw, she isn't that bad." He swallowed. "Um... so... thank you... um... for agreeing to meet up."

Pitch nodded. "Welcome. So, what did you want to do?"

A small frost covered Jack's face. "Oh... uh... well, I didn't actually plan anything. I just wanted to spend time with you."

Pitch nodded. "Okay. Well, how about we go for a walk? It is a nice day."

Jack nodded. "Okay."

"So, what was that before?"

"Huh? What was what?"

"Your face. The ice."

"Oh, that's just my blush."

Pitch nodded. "Huh."

Jack peered up at Pitch. "So... what do you like doing? Besides terrorizing kids and keeping me in a job?"

Pitch actually chuckled at Jack, which made Jack smile a little. "Well, Frost, I think the thing I enjoy most is walking around here. Its... a different feeling. Like being peaceful. It is almost enough to make me remember my past."

"Your past?"

"Yes. Before I was Pitch Black."

"What?"

He looked at Jack. "Just as you were someone before you were Jack Frost, I was someone before I was Pitch Black."

"Whoa. I never knew."

"Hm."

"Sorry" he looked at the ground.

"Don't apologize."

Jack peered up at him. "Wh-?"

"I don't want you to apologize for curiosity."

Jack nodded.

"Not going to ask?"

Jack wanted to. He was more than curious. But he knew that now wasn't the time to ask. "No. When you are ready to talk about it."

Pitch seemed surprised.

"I don't want... I mean... bringing up the past can be... painful. I was lonely for so long... before I was a Guardian. I didn't remember my past at all... then... when I got my memories and found out who I was..." he smiled. "I was so excited. I mean... it was amazing to remember. But then... that brings its own sadness. I will never see my sister again. Its been so long... all I want to do is talk to her once more, tell her that I am okay..." he sighed. "But I can't. She is gone."

Pitch nodded. "Yes... losing family is hard." He looked towards Burgess. "The children you care so much about... are older now. How does that make you feel?"

"Happy. I feel happy. I want them to be happy." He smiled. "Yeah."

"Interesting. Are you ever worried that they will forget you?"

"No. I guess... I don't think about it that way. I mean... they know that I exist..." he chewed his lip. He hadn't really thought about it like that before. Would they one day just not talk to him? Forget about him?

Pitch watched him with intrigue.

Jack shook away the thoughts. "I guess... that is there choice. I have no say in it."

Pitch nodded. "Fair enough."

Jack sighed.

"Not enjoying your time?"

"No, it isn't that... I think I am over-thinking everything."

"I apologize. You don't look like someone who would enjoy over-thinking."

Jack looked up at him, brows furrowed. "Are you trying to insult me?"

"Take it however you like."

Jack bit his lip. He should have known that Pitch hadn't really wanted to speak with him. This day was going downhill fast and it was getting awkward. "Um... I should get going" he muttered.

Pitch was slightly taken aback. "Oh, okay. Well, thank you for joining me."

Jack nodded. He took the wind back to North's.

Tooth was sitting there with Sandy and Bunny, which surprised Jack.

"How did it go?" she asked immediately, fluttering towards him.

"Good" he managed, hoping it didn't sound like a lie. "I'm going to lie down."

"Oh, okay. You rest up now."

He waved and walked down to his room.

"You're such a mum" Bunny sighed. "I have a feeling it didn't go to plan."

She looked at Bunny. "I am going to see Pitch and work this out."

Bunny sighed. "Okay."

"And you're coming with me.'

"No, I am going back to the Warren. Jack started this."

"Actually, you did. You came to me with this information."

He groaned. "Tooth, let's just leave it."

"No. I need answers. I'll catch you both later."

Sandy smiled at her determination and waved her off. Bunny rolled his eyes, opening a tunnel to the Warren and disappearing.

...

Tooth landed at the Burgess forest and saw Pitch standing near Jack's lake. "Pitch! What did you say to Jack?!" she yelled, feeling strongly protective.

He stepped back, surprised. "Nothing. I swear. He just up and left."

She frowned. "But he looked... he came back and he looked like he had a terrible time."

Pitch sighed. "I am not good company. I don't know what he expected from me."

She walked closer. "I... I'm sorry. I really thought you two would have an amazing day." She sighed. "I just wanted you two to be happy together."

"I appreciate your attempts, but I do think that Frost and I... aren't going to work out."

She sighed. "Maybe I shouldn't have meddled."

He shrugged. "Either way, I don't think... this would have worked. Jack can do better."

"But I don't know if he wants to do 'better', rather, I think he just wants to be with someone who he loves for who they are. He likes you a lot. I know that deep down you're lonely. What happened to Lady Pitchiner and Emily Jane- Mother Nature..." she looked away. "I'm sorry. I shouldn't bring it up..." he fiddled with her hands. "I just want you to know that.. Jack is wonderful. He is loving, fun and caring... and he is loyal. I know that you aren't interested, but..." she sighed. "If you ever consider being in a relationship with him, you have my support. I'll let you go." When he said nothing she flew back to the Pole.

...

Jack was surprised when Pitch showed up in the Pole. He was even more surprised that North walked him in, the two having a totally normal conversation. Like the two of them were old friends.

"Ah, Jack, good to see you" North said, as if they hadn't just eaten together an hour ago. "Pitch is here to see you.

"Good morning Jack."

"Pitch... hi... how are you?"

"Good." He looked at North who nodded at him and walked out.

Jack bit his lip. He wanted to say something, anything, but he had no idea what to say. They hadn't exactly ended their 'date' on good terms last week.

Pitch watched Jack, seeing if he would say anything, when Jack didn't he decided to take the next step. "I wanted to firstly apologize for the other day. It wasn't my intention to make you upset... and I have done some reflecting. I would like to let you know that I would like to consider your offer..."

Jack gave him a blank stare, not entirely comprehending.

"I would like to date you" Pitch said. "I think it would be good for both of us."

Jack smiled. "You mean it?"

"I do. I mean every bit of it."

Jack held Pitch's hands in his. "Thank you."

"No need to thank me. I just... I think we need each other."

Jack nodded. "Yeah. I think we do."


End file.
